In this On Purpose episode, Jay Shetty welcomes Ally Webb, founder of Drybar and author of The Messy Truth.

Her accomplishments include the success of Drybar, co-founding Squeeze, and her recent venture, Beckett and Quill. She is also the president of Canopy. 

The episode highlights the importance of maintaining personal well-being while pursuing success in various aspects of life. They discuss Webb's journey from building a multimillion-dollar business to nearly losing herself. 

An Unlikely Entrepreneur

Webb shared her unexpected entrepreneurial journey with Jay Shetty. After getting married and becoming a stay-at-home mom, she wanted to do something for herself. About a year before starting Drybar, she launched a mobile blowout business, providing hair styling services to clients in their homes. 

The new business allowed her to break free from the daily routine of being a stay-at-home mom and engage with adults. Charging $40 per service provided an extra income. Though it started as a small and straightforward venture, it was a stepping stone for what would eventually become Drybar.

Webb's mobile business gained popularity through word of mouth, with clients recommending her to friends. During this time, she recognized the demand for professional hair styling services and the potential to build a larger business. To accommodate her growing clientele, she decided to have clients come to her, leading to the inception of Drybar. Initially, she operated as a one-woman show, traveling around Los Angeles with her tools and products to provide hairstyling services.

Webb never foresaw this journey when she started her mobile blowout business. Her path as an entrepreneur was driven by a desire for personal fulfillment and connection with others. Her intuition and willingness to listen to her inner voice guided her. Financial gain wasn't her primary motivation; instead, it was a genuine passion for her craft and a desire to boost women's confidence.

Success often emerges from unexpected beginnings and personal journeys rather than following a conventional or prescribed path. It is, therefore, essential to trust your instincts and embrace the challenges of entrepreneurship. Regardless of background, anyone can succeed by staying true to themselves and their passions.

Dream Big

Webb shared with Jay Shetty her entrepreneurial journey's deeper aspects, emphasizing the role of intuition and intention. She began with a mobile blowout business, driven by a desire to do something for herself while being a stay-at-home mom. She gradually realized the potential for something more significant as clients and demand grew.

Taking baby steps and not immediately aiming for grandiose success is crucial. Webb focused on what felt right at each stage, allowing her to build a successful business organically. She told Jay Shetty that chasing money should not be the primary motivation and that true success often stems from doing what one loves.

According to Webb, there is a difference between intuition and delusion. She explained to Jay Shetty that intuition involves:

  • Paying close attention to how something makes you feel in the moment.
  • Trusting your inner guidance.
  • Staying close to your authentic self.

On the other hand, delusion involves ignoring red flags and mindlessly pursuing a path despite signs indicating otherwise.

Webb discussed the importance of learning from mistakes and embracing life's challenges as opportunities for growth. Getting older and wiser made her more aware of her instincts and intuition, helping her make better decisions. Spirituality and meditation also played an essential role in enhancing her awareness and intuition.

Developing a Skill Set

Alli Webb and Jay Shetty focused on finding your skill set and having the courage to follow your passion. Webb emphasizes that despite the challenges and competition in the entrepreneurial world, success always starts with the individual – their idea, skills, purpose, and gut instinct.

Webb highlights the importance of recognizing and valuing your unique skills, even if they come naturally and seem effortless. She suggests that many people undervalue their skills because they believe they should be challenging themselves more or pursuing what others perceive as valuable skills.

Jay Shetty warns the listeners not to become someone else's story and to refrain from imitating other entrepreneurs. Webb encourages the audience to pay attention to the voices they might be ignoring within themselves, to reflect on what they genuinely love and feel passionate about, and to avoid being swayed by external opinions and societal expectations.

Initially, Webb dismissed her passion for hair but decided to attend beauty school despite familial skepticism. She recalls moments of self-doubt but ultimately pursued what she loved, believing in her vision. 

She discusses with Jay Shetty the challenges of starting Drybar during a recession and facing skepticism from potential investors who questioned the concept's viability. Yet her determination and willingness to take risks were critical factors in her success.

Imposter Syndrome

Alli Webb shares her perspective on imposter syndrome with Jay Shetty. She views it as a natural part of growth and learning, especially when entering new roles or ventures. Many people talk about imposter syndrome as if it's a detrimental feeling, but she believes it can be beneficial. It signifies that you are stepping out of your comfort zone, taking on new challenges, and embarking on a growth journey. 

Webb emphasizes the importance of having a beginner's mindset. It means being open to learning and not feeling the need to have all the answers as a leader. Webb used to carry the weight of needing to know everything because she was the boss, but in the meantime, she has shifted her approach. She now encourages open dialogue and values input from others, creating a culture where team members feel comfortable sharing their ideas and perspectives.

Open to Feedback

Alli Webb and Jay Shetty delve into the importance of openness to personal and professional feedback. To the entrepreneur, it is a valuable gift rather than something negative. She welcomes feedback and is receptive to what others say.

Webb recalls a memorable feedback she received from her brother, which initially took her by surprise. He mentioned that people were scared of her, and she was initially defensive, questioning why that would be the case. However, she eventually reflected on it and realized that her intense passion and perfectionism could intimidate others.

Feedback can be challenging to hear, but viewing it as an opportunity for growth is essential. Webb learned that feedback could lead to self-awareness and personal development. She also acknowledges the importance of not surrounding herself with "yes" people but rather individuals who are willing to provide honest feedback.

Business vs. Marriage

Webb reflects on her first marriage, which ended after 16 years. She told Jay Shetty that the divorce wasn't directly related to her business success. She acknowledges that her first marriage probably shouldn't have happened in the first place, and she realized that they were more like best friends than intimate partners. 

Webb explains to Jay that she was initially concerned about disrupting her image. Still, eventually, she made the difficult decision to end the marriage. It was challenging to hold both aspects together, and she often focused on one at the expense of the other. 

A Balanced Life

Finding the right balance between material success and a happy personal life can be challenging. Webb expresses her curiosity about whether it's possible to be in love, have a successful relationship, and simultaneously maintain her purpose and projects. Relationships involve two evolving minds, which don't always change or grow in sync. People have different aspirations, dreams, and daily experiences, making it natural to develop in different directions.

Jay Shetty introduces two thought experiments to help people navigate relationships. First, he suggests having the right conversations with yourself and your partner is essential. Without these conversations, everything can feel like a surprise, leading to random events and unexpected outcomes. 

Second, he discusses the concept of balance and how it's essential to recognize that we have finite resources, energy, and time to allocate to different aspects of life. Striving for perfection in all areas is impossible. Instead, individuals should monitor whether they are getting closer or further apart in their relationships and areas of focus.

Communication and honesty with yourself and your partner are paramount. Not addressing issues and avoiding difficult conversations can lead to future challenges and potentially the end of a relationship.

Adults Change, Too

Jay outlines four types of check-ins he practices with his wife, tracking the alignment of their relationship. They include:

  • Daily reflections on highlights.
  • Weekly or monthly discussions of struggles and needs.
  • Quarterly assessments of the relationship's direction.
  • Yearly goal-setting conversations.

Jay Shetty and Alli Webb recognize the human tendency to slip into complacency, where people might stop practicing regular check-ins, leading to a loss of connection and understanding in the relationship. They stress the significance of self-awareness and maintaining daily practices that nurture personal growth and spirituality.

Divorce Aftermath

Alli Webb opens up to Jay Shetty about her experiences with divorce and the emotional challenges it brings. She reflects on the shame and guilt often associated with divorce and how some people avoid it because of fear of judgment. She shares her journey through two divorces, highlighting the complexities of emotions involved in such life-changing events.

Webb discusses the profound impact of divorce on her identity and the initial denial of its significance, comparing it to death in terms of the void it leaves. Community and friends played an important role, providing support and reassurance during difficult times, helping her believe she would eventually be okay.

Jay Shetty emphasizes the importance of seeking support and turning towards positive influences during challenging times. The intersection of unexpected events and familiar feelings can lead to trauma. That's why processing grief and allowing yourself to heal is crucial.

Take Your Time with Relationships

Alli Webb reflects on how she rushed into her marriage because she feared being alone and desired to be in a relationship. She tells Jay Shetty that she realizes the importance of being open and honest about her needs and how vital it is to level set and communicate effectively with a partner.

Webb's major lesson from her first marriage is the significance of accepting imperfections and understanding that nothing is ever perfect. She wanted more from her career and relationship in her second marriage, realizing it's okay to desire more and not settle for less.

Jay Shetty highlights that pursuing a perfect relationship or life is an unrealistic expectation perpetuated by societal narratives. He emphasizes the importance of unlearning these conditioned beliefs, adopting a mindset that embraces imperfections, and acknowledging that perfection is not attainable.

People often project a curated, idealized image of their lives. Still, in reality, everyone faces challenges and imperfections. We often experience sadness or challenges differently than when watching a movie. By adopting the perspective that life is like a movie, we can better understand and accept the ups and downs, realizing that emotions are temporary and our narratives are complex and constantly evolving.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode on “Alli Webb ON How to Embrace Imposter Syndrome & Ways to Take Small Steps Towards Big Success” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at

Jay Shetty On Purpose Podcast
Feeling a little lost lately?

Take my new quiz to discover your deeper purpose.

Take the Quiz
Jay Shetty On Purpose Podcast

Looking for greater meaning? This quiz shows you how to live with purpose every day.

Take the Quiz
Jay Shetty On Purpose Podcast

Dreaming of becoming a life coach? This quiz tells you if a coaching career is right for you.

Take the Quiz
Jay Shetty On Purpose Podcast

Dreaming of becoming a life coach? This quiz tells you if a coaching career is right for you.

Take the Quiz
Jay Shetty On Purpose Podcast

Everyone communicates differently. Discover your own personal fight style now.

Take the Quiz
Jay Shetty On Purpose Podcast

Understanding your role in a relationship is the first step to making things work.

Take the Quiz